Comparison of the conformational properties of carbasugars and glycosides: the role of the endocyclic oxygen.

Carlos Mayato, Rosa L Dorta, José M Palazón, Jesús T Vázquez

Instituto Universitario de Bio-Orgánica Antonio González, Departamento de Química Orgánica, Universidad de La Laguna, Avda. Astrofísico Francisco Sánchez, 2, 38206 La Laguna, Tenerife, Spain.

Carbohydrate research 2012 May 1

filter terms:

A series of carbasugars were prepared and their conformational properties studied by means of NMR spectroscopy. The results were compared to those previously found for O-, S-, and C-β-glycoside analogs. While the rotational populations of the hydroxymethyl group in O-, S-, and C-glycosides are known to depend on the structural nature of their aglycon, in carbasugars it proved to be independent of the pseudo-aglycon. This result confirms that endocyclic oxygen is necessary for the observed relationship between the structure of the aglycon and the rotational populations of the hydroxymethyl group, and indicates that the stereoelectronic exo-anomeric effect is mainly responsible for such conformational dependence. Copyright © 2012 Elsevier Ltd. All rights reserved.

Citation

Carlos Mayato, Rosa L Dorta, José M Palazón, Jesús T Vázquez. Comparison of the conformational properties of carbasugars and glycosides: the role of the endocyclic oxygen. Carbohydrate research. 2012 May 1;352:101-8